(3aS)-1-(2-methylphenyl)-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

• ChemBase ID: 144984
• Molecular Formular: C24H24BNO
• Molecular Mass: 353.26446
• Monoisotopic Mass: 353.19509479
• SMILES: B1(N2CCC[C@H]2C(O1)(c1ccccc1)c1ccccc1)c1ccccc1C
• Canonical SMILES: Cc1ccccc1B1OC([C@H]2N1CCC2)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C24H24BNO/c1-19-11-8-9-16-22(19)25-26-18-10-17-23(26)24(27-25,20-12-4-2-5-13-20)21-14-6-3-7-15-21/h2-9,11-16,23H,10,17-18H2,1H3/t23-/m0/s1
• InChIKey: XHMKFCAQQGBIPZ-QHCPKHFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aS)-1-(2-methylphenyl)-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole
• IUPAC Traditional name: (3aS)-1-(2-methylphenyl)-3,3-diphenyl-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole
• Synonyms: (S)-(-)-3,3-Diphenyl-1-o-tolyl-tetrahydropyrrolo(1,2-c)(1,3,2)oxazaborole solution; (S)-(-)-o-Tolyl-CBS-oxazaborolidine solution; (S)-(-)-3,3-二苯基-1-邻甲苯基-四氢吡咯并(1,2-c)(1,3,2)噁唑硼烷 溶液; (S)-(-)-邻甲苯基-CBS-噁唑硼烷 溶液

Database IDs

• CAS Number: 463941-07-3
• MDL Number: MFCD07369782
• PubChem SID: 162239195; 24884027
• PubChem CID: 11204435

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.48466
• LogD (pH = 7.4): 6.6680694
• Log P: 6.7561
• Molar Refractivity: 105.684 cm^3
• Polarizability: 43.332806 Å^3
• Polar Surface Area: 12.47 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Flash Point: 45 °F; 7 °C
• Density: 0.9009 g/mL at 25 °C

Safety Information

• European Hazard Symbols: Flammable (F); Harmful (Xn)
• UN Number: 1294
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-38-48/20-63-65-67
• Safety Statements: 36/37-62
• RID/ADR: UN 1294 3/PG 2

Product Information

• Concentration: 0.5 M in toluene
• Empirical Formula (Hill Notation): C24H24BNO

DETAILS

Sigma Aldrich - 654302

Application
When protonated with trifluoromethanesulfonimide, chiral oxazaborolidines generate chiral Lewis acids, which have demonstrated great utility in the enantioselective Diels-Alder reaction.1,2
CBS Catalysts for Asymmetric Reduction and Asymmetric Synthesis
Packaging
5, 25 mL in glass bottle